Pyridine-N-oxide-substituted salicylaldehyde or salicyclic acid derivatives, their preparation and their use as herbicides

A pyridine-N-oxide substituted salicylaldehyde or salicylic acid of the formula I ##STR24## where R is a group ##STR25## where R.sup.1 has the following meanings:

• a) hydrogen;
• b) a succinylimidoxy group;
• c) a pyrrolyl, pyrazolyl, imidazolyl or triazolyl group linked via a nitrogen atom, which can carry one to two halogen atoms and/or one to two of the following radicals:
• C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;
• d) a radical --(O).sub.m --NR.sup.6 R.sup.7, where m is 0 or 1 and R.sup.6 and R.sup.7, which can be identical or different, have the following meanings:
• hydrogen;
• C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, these radicals in each case being able to carry one to five halogen atoms and/or one to two of the following groups:
• C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.3 -C.sub.6 -alkenylthio, C.sub.3 -C.sub.6 -alkynylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.3 -C.sub.6 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl, C.sub.3 -C.sub.6 -alkynyloxycarbonyl, di-(C.sub.1 -C.sub.4 -alkyl)amino, C.sub.3 -C.sub.8 -cycloalkyl, phenyl or phenyl which is mono- or polysubstituted by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;
• phenyl, which can be substituted by one or more of the following radicals:
• halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;
• R.sup.6 and R.sup.7 together are an unsubstituted or substituted C.sub.4 -C.sub.7 -alkylene chain closed to give a ring, selected from the group consisting of --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.6 --, --(CH.sub.2).sub.7, --CH.sub.2 --CH.dbd.CH--CH.sub.2 --, and --CH.dbd.CH--(CH.sub.2).sub.3 -- or together are an unsubstituted or substituted C.sub.3 -C.sub.6 -alkylene chain which contains a heteroatom and is closed to give a ring, selected from the group consisting of --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --, --CH.sub.2 --S--(CH.sub.2).sub.3 --, --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.3 --, --NH--(CH.sub.2).sub.3, --CH--NH--(CH.sub.2).sub.2 --;
• e) R.sup.1 is additionally a group ##STR26## where R.sup.8 is C.sub.1 -C.sub.4 -alkyl, phenyl, phenyl which is mono- or polysubstituted by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, p assumes the values 1, 2, 3 or 4 and k assumes the values 0, 1 or 2;
• f ) a radical OR.sup.9, where R.sup.9 is:
• i) hydrogen, an alkali metal cation, the equivalent of an alkaline earth metal cation, the ammonium cation or an organic ammonium ion;
• ii) a C.sub.3 -C.sub.8 -cycloalkyl group, which can carry one to three C.sub.1 -C.sub.4 -alkyl radicals;
• iii) a C.sub.1 -C.sub.8 -alkyl group, which can carry one to five halogen atoms and/or one of the following radicals:
• C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, cyano, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenyl, or phenyl or phenoxy which is mono- or polysubstituted by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;
• iv) a C.sub.1 -C.sub.8 -alkyl group, which can carry one to five halogen atoms and carries one of the following radicals:
• a 5-membered heteroaromatic selected from the group consisting of pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, benzotriazolyl, isoxazolyl, oxazolyl and thiazolyl, bonded via a C atom or, if possible, an N atom, which can carry one to four halogen atoms and/or one to two of the following radicals:
• nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;
• v) a C.sub.2 -C.sub.6 -alkyl group, which in the 2-position carries one of the following radicals:
• C.sub.1 -C.sub.4 -alkoxyimino, C.sub.3 -C.sub.6 -alkenyloxyimino, C.sub.3 -C.sub.6 -haloalkenyloxyimino or benzyloxyimino;
• vi) a C.sub.3 -C.sub.6 -alkenyl group or a C.sub.3 -C.sub.6 -alkynyl group, where these groups in turn can carry one to five halogen atoms;
• vii) a phenyl radical which can carry one to five halogen atoms and/or one to three of the following radicals:
• nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;
• viii) a 5-membered heteroaromatic selected from the group consisting of pyrazolyl, imidazolyl, benzimidazolyl, triazolyl and benzotriazolyl and linked via a nitrogen atom which can carry one to two halogen atoms and/or one to two of the following radicals:
• nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;
• ix) R.sup.9 is additionally a group --N.dbd.C--R.sup.10 R.sup.11, where R.sup.10 and R.sup.11, which can be identical or different, are:
• C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, these radicals being able to carry a C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio radical and/or a phenyl radical;
• phenyl which can be substituted by one or more of the following radicals:
• halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;
• or R.sup.10 and R.sup.11 together form a C.sub.3 -C.sub.12 -alkylene chain which can carry one to three C.sub.1 -C.sub.4 -alkyl groups;
• g) or R.sup.1 forms a radical --NH--SO.sub.2 R.sup.12, where R.sup.12 is:
• C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, these radicals being able to carry a C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio radical and/or a phenyl radical;
• phenyl which can be substituted by one or more of the following radicals:
• halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;
• R.sup.2 is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;
• X is CR.sup.13, R.sup.13 being hydrogen or halogen or together with R.sup.3 forming a 3- to 4-membered alkylene or alkenylene chain in which one methylene group in each case is replaced by oxygen, such chain selected from the group consisting of --CH.sub.2 --CH.sub.2 --O--, --CH.dbd.CH--O--, --CH.sub.2 --CH.sub.2 --CH.sub.2 --O-- and --CH.dbd.CH--CH.sub.2 --O--;
• R.sup.3 is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio, or R.sup.3 is linked with R.sup.13 as indicated above to give a 5- or 6-membered ring;
• Y is oxygen or sulfur;
• R.sup.14 -R.sup.17 are
• a) a C.sub.3 -C.sub.8 -cycloalkyl group, which can carry one to three C.sub.1 -C.sub.4 -alkyl radicals;
• b) a C.sub.1 -C.sub.8 -alkyl group, a C.sub.1 -C.sub.8 -alkoxy group or a C.sub.1 -C.sub.4 -alkylthio group, the groups mentioned in each case being able to carry one to five halogen atoms and/or one of the following radicals:
• C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, cyano, C.sub.3 -C.sub.8 -cycloalkyl or di-C.sub.1 -C.sub.4 -alkylamino;
• c) a di-C.sub.1 -C.sub.4 -alkylamino or a di-C.sub.1 -C.sub.4 -alkylaminoxy group;
• d) a C.sub.2 -C.sub.6 -alkenyl group or a C.sub.2 -C.sub.6 -alkynyl group, which can carry one to five halogen atoms and/or one of the following radicals:
• C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;
• e) hydrogen, halogen, nitro or cyano.